Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson

By Richard S. Monson

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Heating the resulting mixture for 1 hour on the steam bath serves to expel most of the ammonia. The reaction mixture is extracted six times with 50-ml portions of ether. The combined extracts are washed twice with water, then with 28 3. DISSOLVING METAL REDUCTIONS 100 ml of 5% hydrochloric acid, again with water, and finally twice with saturated sodium chloride solution. After removal of the ether on the steam bath, the brown residue is taken up in 45 ml of glacial acetic acid. 8 g of chromic anhydride dissolved in the minimum amount of water.

The resulting solution is diluted with 65 ml of water, ammonium sulfate (20 g) is added, and the mixture is extracted with four 100-ml portions of ether. The combined extracts are washed three times with 30-ml portions of water and dried over anhydrous magnesium sulfate. 4194, in about 90% yield. REFERENCES 1. N. G. " Interscience, New York, 1956; W. G. Brown, Org. React. 6, 469 (1951). 2. A. I. Vogel, "Practical Organic Chemistry," 3rd ed. Longmans, London, 1956. 3. W. G. Dauben, R. C. Tweit, and R.

The melting point varies with the purity of the starting diene but is usually above 65°. II. , 100 atm) and high temperatures. However, the development of rhodium catalysts has alleviated these difficulties, allowing the low-pressure (50 psi) hydrogenation of phenols without attendant hydrogenolysis. , hydrogen-oxygen or methanol-oxygen) is to be avoided. Mild evacuation of the reaction vessel containing the catalyst prior to the introduction of hydrogen, and the flushing and evacuation of the vessel several times with hydrogen at low pressure will serve to prevent any difficulties.

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